2732-18-5

Basic information

• Product Name: 5,7-DIHYDROXYCOUMARIN
• Synonyms: 5,7-DIHYDROXYCOUMARIN;2H-1-Benzopyran-2-one, 5,7-dihydroxy-;5,7-Dihydroxy-2H-1-benzopyran-2-one;5,7-Dihydroxy-2H-chromen-2-one
• CAS NO: 2732-18-5
• Molecular Formula: C₉H₆O₄
• Molecular Weight: 178.14
• Mol File: 2732-18-5.mol

Chemical Properties

• Melting Point: 280 °C
• Boiling Point: 506.402 °C at 760 mmHg
• Flash Point: 216.911 °C
• Appearance: /
• Density: 1.563 g/cm³
• Vapor Pressure: 7.06E-11mmHg at 25°C
• Refractive Index: 1.689
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.18±0.20(Predicted)
• CAS DataBase Reference: 5,7-DIHYDROXYCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-DIHYDROXYCOUMARIN(2732-18-5)
• EPA Substance Registry System: 5,7-DIHYDROXYCOUMARIN(2732-18-5)

Safety Data

• Hazardous Substances Data: 2732-18-5(Hazardous Substances Data)

Usage

Uses

Used in Coatings Industry:
5,7-Dihydroxycoumarin is used as a UV-responsive agent for the development of controlled-release and self-repairing antifouling paint. Its photoresponsive nature allows it to undergo structural changes upon exposure to ultraviolet light, enabling the controlled release of active ingredients and facilitating self-healing properties in the paint. This application is particularly beneficial in marine and industrial settings, where fouling and wear are common issues.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 41, p. 4542, 1998 DOI: 10.1021/jm981032oJournal of Heterocyclic Chemistry, 2, p. 91, 1965 DOI: 10.1002/jhet.5570020116

InChI:InChI=1/C9H6O4/c10-5-3-7(11)6-1-2-9(12)13-8(6)4-5/h1-4,10-11H

Upstream product

• 21524-17-4 5,7-diacetoxyl-2-chromenone 
• 108-73-6 3,5-dihydroxyphenol 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 84740-26-1 6-(C-β-D-glucosyl)-5,7-dihydroxycoumarin 
• 623-47-2 propynoic acid ethyl ester 
• 471-25-0 Propiolic acid 
• 882685-19-0 (E)-3-(2,4,6-trihydroxyphenyl)acrylic acid octyl ester 
• 487-70-7 2,4,6-trihydroxybenzaldehyde 
• 1185256-07-8 ethyl (2E)-3-(2,4,6-trihydroxyphenyl)arylate 
• 922-67-8 propynoic acid methyl ester 

Downstream Products

• 487-06-9 Limettin 
• 57601-61-3 6,6,10,10-tetramethyl-2H,6H,10H-benzo<1,2-b:13,4-b':5,6-b''>tripyran-2-one 
• 31525-75-4 5-hydroxy-8,8-dimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one 
• 106726-12-9 5-hydroxy-10,10-dimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one 
• 21524-17-4 5,7-diacetoxyl-2-chromenone 
• 3067-10-5 7-hydroxy-5-methoxychromene-2-one 
• 23053-61-4 5,7-dihydroxycoumarin 7-methyl ether 
• 7758-73-8 5,7-dihydroxy-4-phenyl-2H-1-benzopyran-2-one 
• 2107-76-8 4-methyl-5,7-dihydroxycoumarin 
• 108-73-6 3,5-dihydroxyphenol 
• 64-19-7 acetic acid 
• 130364-30-6 7-hydroxy-5',5a'-dimethylpyrano[2',3'-f]-(2H)-chromen-2-one 
• 33899-44-4 5-(2-enyl-3-methylbut)oxy-7-hydroxycoumarin 
• 31525-76-5 5-methoxyseselin 

Relevant articles and documents

Evaluation of coumarin and neoflavone derivatives as HCV NS5B polymerase inhibitors

Coumarins and coumestans represent an important family of compounds with diverse pharmacological properties. We recently identified coumestans as novel inhibitors of hepatitis C virus NS5B polymerase and predicted their binding in thumb pocket-1 (TP-1) of NS5B. As the coumarins are structurally related to coumestans by virtue of their common A- and B-rings, we postulated them to also exhibit similar binding interaction with NS5B and inhibit its polymerase function. We therefore investigated 24 coumarin and neoflavone derivatives as candidate NS5B inhibitors and identified 14 compounds inhibiting NS5B polymerase activity with IC50 values between 17 and 63 μm. Of these, the newly synthesized 6,8-diallyl-5,7-dihydroxycoumarin (8a) was produced in three steps in high chemical yield from floroglucinol and found to be the most potent of this series, exhibiting activity similar to the reference coumestan LQB-34. The binding site of 8a was mapped to TP-1 of NS5B by counter screening against P495L NS5B mutant, employed as a screen for TP-1 site binders. NS5B-TP-1-8a interaction map provided insight into 8a binding and offered clues for future SAR optimization.

1H AND 13C NMR SPECTRA AND THE STRUCTURE OF A NEW COUMARIN, C-GLYCOSIDE DAUROSIDE D, FROM Haplophyllum dauricum

On the basis of chemical transformation, 1H and 13C NMR spectra, tha structure of dauroside D isolated from Haplophyllum dauricum has been established as 6-C-β-D-glucopyranosyl-5,7-dihydroxycoumarin.Some interesting features of the 1H NMR spectra of its acetate have reported and an assignment of the signals in its 1H and 13C NMR spectra has been made.Dauroside D is the first natural coumarin C-glycoside.

Use of microwave irradiation and solid acid catalysts in an enhanced and environmentally friendly synthesis of coumarin derivatives

Condensation of phenol, 1,3-dihydroxybenzene and 1,3,5- trihydroxybenzene with propynoic and propenoic acids and ethyl acetoacetate using solid acid catalysts and microwave irradiation produces coumarins in excellent yields. The use of heterogeneous catalysts eliminates the production of acidic waste streams associated with conventional (Lewis) acid catalysts. This quick, efficient and environmentally friendly procedure permits the synthesis of substituted coumarins as well as coumarins without 4-alkyl substituents, which are the most difficult to synthesize.

Biomimetic Synthetic Studies on the Bruceol Family of Meroterpenoid Natural Products

A biomimetic approach to total synthesis can offer several benefits, including the development of cascade reactions for the rapid generation of molecular complexity, and guidance in the structure revision of old natural products and the anticipation of ne

Palladium(II)-catalyzed efficient synthesis of wedelolactone and evaluation as potential tyrosinase inhibitor

Tyrosinase is an enzyme widely distributed in nature, which has multiple functions, especially in the melanin biosynthesis pathway. Despite the few clinically available tyrosinase inhibitors for whitening, a great demand remains for novel compounds with low side effects in terms of potential carcinogenicity and improved clinical efficacy. A natural product, wedelolactone (WEL), with a polyhydroxyl moiety, attracted our attention as a potential tyrosinase inhibitor. Before we studied the biological activity of the natural product, a synthetic methodological research was firstly carried to obtain enough raw material. WEL could be obtained efficiently through palladium-catalyzed boronation/coupling reactions and 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ)-involved oxidative deprotection/annulation reactions. Immediately after, the natural product was proven to be an efficient tyrosinase inhibitor. In conclusion, we developed a mild and efficient approach for the preparation of WEL, and the natural product was disclosed to have anti-tyrosinase activity, which could be widely used in multiple fields.

Difluoromethylthiolation of Phenols and Related Compounds with a HF2CSO2Na/Ph2PCl/Me3SiCl System

A novel HF2CSO2Na/Ph2PCl/Me3SiCl system is disclosed for the late-stage direct difluoromethylthiolation of Csp2 and Csp3 nucleophiles. Difluoromethylthiolation of phenols and naphthols proceeded nicely under this system to regioselectively provide corresponding SCF2H compounds in good yields. Other substrates such as indoles, pyrroles, pyrazoles, enamines, ketones, and β-keto esters were also transformed to corresponding SCF2H products in good yields. The late-stage direct difluoromethylthiolation of a number of natural products and pharmaceutically attractive molecules was also achieved.

Structures of antimutagenic constituents in the peels of Citrus limon

The methanolic extracts from the peels of Citrus limon were found to show antimutagenic effects against 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole, and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in the Ames test. From the methanolic extracts, four new coumarins (wakayamalimonol A–D) and a new furanocoumarin (wakayamalimonol E) were isolated together with fifteen known compounds. The absolute stereostructures of the new compounds were determined by chemical synthesis and the modified Mosher’s method. Among the isolated constituents, coumarins, furanocoumarins, and limonoids showed antimutagenic effects in the Ames test. One of the major constituent, limonin, showed significant antimutagenic effects against mitomycinC and PhIP in the micronucleus test in vivo.

Ytterbium triflate promoted coupling of phenols and propiolic acids: Synthesis of coumarins

Coumarins are a well-known class of natural occurring and semi-synthetic products with reported important and effective pharmacological activities. In this Letter an improved method for the chemical synthesis of such compounds is described. Coumarins have been obtained in good to excellent yields under microwave irradiation and solvent-free conditions in a short time from differently substituted phenols and propiolic acids used as starting materials in the presence of Yb(OTf)3 hydrate 10% mol as the catalyst.

A Total Synthesis of (±)-Rhododaurichromanic Acid A via an Oxa-[3+3] Annulation of Resorcinols

Development of an oxa-[3+3] annulation of vinyliminium salts with resorcinols as a 1,3-diketo equivalent is described. This annulation constitutes a cascade of Knoevenagel condensation-oxa-electrocyclization leading to a direct access to chromenes. A series of attempts was made to demonstrate its synthetic utility in natural product synthesis, culminating in a total synthesis of (±)-rhododaurichromanic acid A that also featured an intramolecular Gassman-type cationic [2+2] cycloaddition.

Synthesis and cytotoxicity of coumarin derivatives and nordentatin

Nordentatin and 10 coumarin derivatives were synthesized and evaluated for cytotoxicity. Compounds 6, 7, 9 and 13 showed cytotoxicity against the NCI-H187 cell line with IC50 value ranging of 3-7 μg/mL. Among synthesized coumarins, compounds 4 and 13 demonstrated cytotoxicity against the KB cell line with IC50 values of 3.94 and 6.44 μg/mL, respectively. Fortunately, coumarins 4 and 7 may be one of the new lead compounds for the development of anticancer agents due to reason that they showed weak and inactive against normal cells.